Controlled Aerobic Oxidation of Primary Benzylic Alcohols to Aldehydes Catalyzed by Polymer-Supported Triazine-Based Dendrimer–Copper Composites

Synlett ◽  
2018 ◽  
Vol 29 (09) ◽  
pp. 1152-1156 ◽  
Author(s):  
Shiguang Pan ◽  
Shuo Yan ◽  
Takao Osako ◽  
Yasuhiro Uozumi
Keyword(s):  
Catalytic Activity ◽  
Ethylene Glycol ◽  
Copper Complexes ◽  
Aerobic Oxidation ◽  
Catalytic Amount ◽  
Significant Loss ◽  
Atmospheric Conditions ◽  
Benzylic Alcohols ◽  
Simple Filtration ◽  
Polymer Supported

A controlled aerobic oxidation of primary benzylic alcohols to the corresponding benzaldehydes by using polystyrene–poly­(ethylene glycol) (PS–PEG) resin-supported triazine-based polyethyleneamine dendrimer–copper complexes [PS–PEG-TD2–Cu(II)] was developed. In particular, PS–PEG-TD2–Cu(OAc)2 efficiently catalyzed the aerobic oxidation of benzylic alcohols in the presence of a catalytic amount of TEMPO under atmospheric conditions to give the corresponding aldehydes in up to quantitative yield. The catalyst was readily recovered by simple filtration and reused four times without significant loss of its catalytic activity.

Studies on Iron-Catalyzed Aerobic Oxidation of Benzylic Alcohols to Carboxylic Acids

Synthesis ◽  
2018 ◽  
Vol 50 (08) ◽  
pp. 1629-1639 ◽  
Author(s):  
Shengming Ma ◽  
Xingguo Jiang
Keyword(s):  
Carboxylic Acids ◽  
Large Scale ◽  
Aerobic Oxidation ◽  
Catalytic Amount ◽  
Steric Effects ◽  
Benzylic Alcohols ◽  
Academic Laboratory ◽  
Electron Donating Groups ◽  
Electronic And Steric Effects ◽  
Comprehensive Study

A comprehensive study on aerobic oxidation of benzylic alcohols­ to carboxylic acids with a catalytic amount each of Fe(NO3)3·9H2O, TEMPO, and KCl is conducted. Various synthetically useful functional groups are well tolerated in the reaction. Distinct electronic and steric effects are observed in the reaction: electron-withdrawing groups accelerate the reaction while electron-donating groups make the reaction slower, and ortho-substituted substrates react slower than meta-substituted substrates. Several large-scale reactions (100 mmol) are conducted using a slow air flow of 30 mL/min to demonstrate the practicality of this method in an academic laboratory.

scholarly journals LiHSO4/SiO2as a New, Efficient and Reusable Catalytic System for the Chemoselective Conversion of Aldehydes to Acylals under Solvent-Free Conditions

2009 ◽  
Vol 6 (s1) ◽  
pp. S390-S396 ◽  
Author(s):  
Abdolkarim Zare ◽  
Alireza Hasaninejad ◽  
Esmael Rostami ◽  
Ahmad Reza Moosavi-Zare ◽  
Maria Merajoddin ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Acetic Anhydride ◽  
Catalytic System ◽  
Catalytic Amount ◽  
Significant Loss ◽  
Solvent Free ◽  
Reaction Conditions ◽  
Highly Efficient ◽  
Solvent Free Conditions

A highly efficient, green and expeditious solvent-free method is described for the chemoselective conversion of aldehydes to the corresponding acylals in excellent yields, using acetic anhydride in the presence of catalytic amount (20 mol%) of silica-supported LiHSO4. Ketones does not react under these reaction conditions. LiHSO4/SiO2can be recovered and reused without any significant loss of its catalytic activity.

Cobalt(II), copper(II), and iron(II) tetrasulfophthalocyanines covalently supported on wool: Synthesis, characterization and catalytic activity

2016 ◽  
Vol 20 (06) ◽  
pp. 677-688 ◽  
Author(s):  
Ahmad Shaabani ◽  
Zeinab Hezarkhani
Keyword(s):  
Catalytic Activity ◽  
Carbonyl Compounds ◽  
Aerobic Oxidation ◽  
Significant Loss ◽  
X Ray Diffraction ◽  
Flame Atomic Absorption Spectroscopy ◽  
X Ray ◽  
Flame Atomic Absorption ◽  
Eds Analysis ◽  
Ft Ir

Functionalized wool with cobalt(II), copper(II), and iron(II) tetrasulfophthalocyanine (CoTSPc@wool, CuTSPc@wool, and FeTSPc@wool) have been synthesized and their structures characterized by flame atomic absorption spectroscopy (FAAS), FT-IR, UV-vis, X-ray diffraction (XRD), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), and the energy dispersive spectroscopy (EDS) analysis. The catalytic activity of the synthesized catalysts was investigated for the aerobic oxidation of alkyl arenes and alcohols to their corresponding carbonyl compounds in the absence of any co-promoter and additional oxidizing reagent. We found the best catalyst for the mentioned reactions is the CoTSPc@wool from the solvent, conversion, temperature, and reaction time point of views. The synthesized catalysts can be readily recycled and reused for several runs without significant loss of efficiency.

An aerobic oxidative synthesis of aryl nitriles and primary aryl amides from benzylic alcohols catalyzed by a polymer supported Cu(ii) complex

2015 ◽  
Vol 39 (2) ◽  
pp. 921-930 ◽  
Author(s):  
Rostam Ali Molla ◽  
Kajari Ghosh ◽  
K. Tuhina ◽  
Sk Manirul Islam
Keyword(s):  
Catalytic Activity ◽  
Catalytic Performance ◽  
Initial Activity ◽  
Benzylic Alcohols ◽  
Aryl Nitriles ◽  
Polymer Anchored ◽  
Polymer Supported

A new polymer anchored Cu(ii) complex has been synthesized and characterized. The catalytic performance of this complex has been tested for the synthesis of nitriles and amides from benzylic alcohols. This catalyst showed excellent catalytic activity, recyclability and could be reused more than five times without appreciable loss of its initial activity.

Zirconium(IV) 4-sulphophenylethyliminobismethylphosphonate as an efficient and reusable catalyst for one-pot synthesis of 3,4-dihydropyrimidones under solvent-free conditions

2011 ◽  
Vol 65 (6) ◽  
Author(s):  
Xin-Bin Yang ◽  
Xiang-Kai Fu ◽  
Yu Huang ◽  
Ren-Quan Zeng
Keyword(s):  
Catalytic Activity ◽  
Elemental Analysis ◽  
Biginelli Reaction ◽  
Significant Loss ◽  
Solvent Free ◽  
Reusable Catalyst ◽  
One Pot ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Simple Filtration

AbstractZirconium(IV) 4-sulphophenylethyliminobismethylphosphonate (ZSBEDP) was prepared and characterised by elemental analysis, IR, TG-DSC, and XRD. ZSBEDP was found to be an efficient catalyst for the Biginelli reaction of aromatic aldehyde, ethyl acetoacetate, and urea or thiourea under solvent-free conditions so as to give 3,4-dihydropyrimidones in good to excellent yields. The catalyst can be separated by simple filtration and reused without significant loss of its catalytic activity.

Enhanced catalytic activity of copper complexes in microgels for aerobic oxidation of benzyl alcohols

2020 ◽  
Vol 56 (42) ◽  
pp. 5601-5604
Author(s):  
Dominic Schäfer ◽  
Fabian Fink ◽  
Denise Kleinschmidt ◽  
Kristina Keisers ◽  
Fabian Thomas ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Copper Complexes ◽  
Aerobic Oxidation ◽  
Benzyl Alcohols ◽  
Catalytically Active

Catalytically active copper bis(pyrazolyl)methane complexes have been anchored into pVCL-GMA microgels on specified positions within the microgel network.

Palladium-catalyzed aerobic alcohol oxidation supported by a new type of α-diimine ligands

2008 ◽  
Vol 86 (8) ◽  
pp. 782-790 ◽  
Author(s):  
Jin Zhou ◽  
Xiaoyan Li ◽  
Hongjian Sun
Keyword(s):  
Catalytic Activity ◽  
Electronic Properties ◽  
Steric Hindrance ◽  
Aerobic Oxidation ◽  
Alcohol Oxidation ◽  
Palladium Complexes ◽  
Benzylic Alcohols ◽  
Diimine Ligands ◽  
Palladium Catalyzed ◽  
New Type

A series of new ionic sulfonated α-diimine ligands were prepared and employed as supporting ligands for the palladium-catalyzed aerobic alcohol oxidation. The electronic properties, rigidity, and steric hindrance of ligands have remarkable influences upon the catalytic activity of the palladium complexes. The best catalytic result could be achieved using ligand 9 with an electron-withdrawing sulfonyl substituent together with bulky groups (iso-propyl in 2,6-positions). This diimine/palladium-catalyzed system is highly efficient for the oxidation of various benzylic alcohols, and showed moderate yields for the secondary aliphatic alcohols and cyclic alcohols.Key words: α-diimine, palladium, aerobic oxidation, alcohol.

Green and efficient synthesis of 1, 2, 4-Triazolidine-3-thiones using guanidine hydrochloride as a recyclable catalyst under the aqueous condition

2022 ◽  
Vol 19 ◽  
Author(s):  
Angad B. Barkule ◽  
Yatin U. Gadkari ◽  
Vikas N. Telvekar
Keyword(s):  
Energy Efficiency ◽  
Catalytic Activity ◽  
Reaction Time ◽  
Guanidine Hydrochloride ◽  
Catalytic Amount ◽  
Significant Loss ◽  
Recyclable Catalyst ◽  
Efficient Synthesis ◽  
Aryl Aldehydes ◽  
Work Up

Abstract: A rapid and highly efficient methodology for the synthesis of 1, 2, 4-Triazolidine-3-thiones derivatives has been developed in the presence of a catalytic amount of guanidine hydrochloride using water as a solvent. The reaction of thiosemicarbazide with different aryl aldehydes resulted in the formation of title compounds in good yields (85% -95%) with a convenient reaction time (20-30 min). The key advantages of this approach are shorter reaction time, energy efficiency, easy work-up procedure, and wide substrate scope tolerance. Further, the catalyst was recycled without significant loss of its catalytic activity

Synthesis and characterization of copper(ii) 4′-phenyl-terpyridine compounds and catalytic application for aerobic oxidation of benzylic alcohols

2014 ◽  
Vol 43 (10) ◽  
pp. 4048-4058 ◽  
Author(s):  
Zhen Ma ◽  
Lijuan Wei ◽  
Elisabete C. B. A. Alegria ◽  
Luísa M. D. R. S. Martins ◽  
M. Fátima C. Guedes da Silva ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Catalytic Activity ◽  
Aerobic Oxidation ◽  
Synthesis And Characterization ◽  
Benzylic Alcohols ◽  
Mild Conditions ◽  
Catalytic Application ◽  
Alkaline Aqueous Solution

Cu(ii)-terpyridine complexes in combination with TEMPO exhibit catalytic activity, under mild conditions and in alkaline aqueous solution, for the aerobic oxidation of benzylic alcohols.

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